2-Pyrazinecarboxylic acid → 4-[3-(2-Pyrazinecarbonylamino)propylthio]pyridine
Reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.ON1C(=O)CCC1=O.Cl.C(N=C=NCCCN(C)C)C.Cl.Cl.[NH2:32][CH2:33][CH2:34][CH2:35][S:36][C:37]1[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=1>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([NH:32][CH2:33][CH2:34][CH2:35][S:36][C:37]1[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=1)=[O:9]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1.00 g (8.06 mmol) of 2-pyrazinecarboxylic acid and 1.21 g (10.5 mmol) of N-hydroxysuccinimide in 70 ml of methylenechloride, 1.85 g (9.67 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was added with stirring under ice-cooling, and the mixture was stirred at room temperature for 1 hour. Further, 1.94 g (8.06 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was washed with saturated aqueous sodium bicarbonate and water, and dried. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate) to give 0.751 g of the desired compound (34.0% yield, colorless powder).
Workup
- temperaturecooling
- stirringthe mixture was stirred at room temperature for 1 hour
- stirringthe mixture was stirred at room temperature for 3 hours
- washThe reaction mixture was washed with saturated aqueous sodium bicarbonate and water
- customdried
- distillationThe solvent was distilled off
- customthe residue was purified by column chromatography (eluent: ethyl acetate)
Sources & evidence
- ORD record
- ord-f208188fc14e4da897c2c1b05194c884
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05389658
Reaction notes
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